Upcoming Events

Embrace the allure of our Eastern Shore haven, where each passing season ushers in its own tapestry of charm and adventure! As we peer into the unfolding year, we're excited to present exciting happenings and unforgettable moments. Whether you're drawn to the vibrant hues of spring's awakening, the spirited festivities of summer's peak, the rustic warmth of autumn's embrace, or the magical enchantment of winter's frost, there's an experience tailored to enchant every soul. Navigate below to find the ideal time to plan your stay.

Winter

Chocolate bark food stand on Talbot Street in St. Michaels

8th Annual St. Michaels ChocolateFest

Indulge your sweet side at ChocolateFest on March 7, 2026! Sample decadent creations from local restaurants and shops, and explore the town while savoring chocolate-inspired delights.

Chesapeake Fire & Ice Festival in Easton

Just a 15-minute drive from St. Michaels in Easton, MD, the Fire & Ice Festival, February 20 & 21, 2026, dazzles with ice sculptures, live music, and seasonal festivities that warm the winter spirit.

Nordic SPA Experience

As a special Valentine’s experience, SPA at Perry Cabin introduces the outdoor Nordic Experience in partnership with Ritual Sauna & Plunge.

Rooted in warmth, release, and presence, this experience invites you to move between a wood-fired sauna and invigorating cold plunges, creating a deliberate contrast that refreshes both body and mind.

Offered in reserved time slots, the Nordic Experience may be enjoyed on its own or paired with SPA treatments, offering a thoughtful way to indulge this Valentine season. The experience is well suited for sharing, whether with a partner or close friends, and may be reserved for up to six guests.

Reserve through Guest Services by phone 443-258-2228 or email [email protected].

JOIN US SUPER BOWL LX

The game’s on, and we’re switching things up for the day. Brats, wings, smash burgers, pretzels, pitchers, and a few drink specials making a special appearance—plus raffle drawings at the end of each quarter. Super Bowl Sunday—less buttoned-up, more game-day.

Santa Claus lighting Christmas lights along the lane

Lighting of the Lane

Join us on Friday, November 28th for the beloved Lighting of the Lane, a cherished tradition that warmly welcomes the holiday season. Guests of the Inn are invited to step into a winter wonderland where snowflakes dance, Santa spreads cheer, and cozy beverages are enjoyed as we count down to the grand unveiling of lights along the lane.

Midnight Madness

Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.

Christmas in St. Michaels

Experience the magic of Christmas in St. Michaels from December 12 - 14! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.

Spring

Market stall with people browsing colorful glass bottles and stones.

Eastern Shore Sea Glass and Coastal Arts Festival

Save the date for the upcoming Eastern Shore Sea Glass and Coastal Arts Festival, taking place Saturday, April 18 and Sunday, April 19, 2026 at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. This Spring Edition promises an extraordinary showcase of coastal craftsmanship, with over 90 exhibitors presenting a diverse collection of jewelry, home décor, art, and more.

St. Michaels WineFest

Sip and explore a wide range of international wines during the Wine Tasting Festival, taking place Saturday, April 25 – Sunday, April 26, 2026. Featuring vineyards from renowned wine regions around the world, the event offers a relaxed way to discover new favorites and enjoy a spring weekend.

Mom and her little ones on a boat charter

Mother's Day

For Mother's Day, celebrate the amazing women who deserve to be pampered! Show your love by gifting them an unforgettable experience at Inn at Perry Cabin, where every moment is wrapped in luxury.

Easter Day Petting Zoo & Pony Rides

Pony rides, a petting zoo, and a very hoppy visitor bring Easter day joy for the whole family. Join us on Linden Lawn from 9:00–11:00 AM as Wild Kid Acres Farm arrives with a mini cow, donkey, pig, goat, chicken, and turkey for up-close springtime fun. Admission is $20 per person, with pony rides available for $15 for one ride or $25 for two rides.

Return of the Fleet

On Saturday, April 11 from 1:00 - 4:00 PM, join us for our most anticipated celebration of the year complete with live music by Justin Ryan throughout the afternoon!

Admission is $25 per person and includes complimentary Veuve Clicquot and fresh shucked Oysters from 2:00–3:30 PM.

At 2:30 PM, the fleet arrives to the sound of bagpipes, marking the return of the season, followed by remarks from Captain Jason and the traditional Blessing of the Fleet.

A cash bar and light bites will be available throughout the afternoon as the music continues until 4:00 PM.

RSVP encouraged as space is limited, 443-258-2228 or [email protected]. Tickets purchased at door.

Easter on the Miles

In addition to pony rides and the petting zoo, the Easter festivities continue with a festive Easter Egg Hunt at 11:00 AM, available exclusively for brunch guests and guests of the Inn. Then, enjoy Easter Day Dining with seatings from 12:00–4:30 PM, and keep an eye out for a very special guest — the Easter Bunny will be hopping around throughout the day, ready for photos, smiles, and a touch of springtime magic.

For dining details, please visit our dining page.

Talbot Humane Paws & Plates

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day! Due to the forecast, Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Join us for Paws & Plates, a dog-friendly evening at the Lighthouse on the Pointe, welcoming locals and visitors alike from 4 to 7 pm. Bring your pup and enjoy live music, our pizza oven, and a wine and beer bar, all while supporting a great cause: 10% of proceeds will benefit Talbot Humane Society. Don’t miss the doggie menu and pop-up shop filled with treats and toys for your four-legged friend!

Sparkling Afternoons

Slide into the spirit of summer with us on Fridays, June 13, and 27, and Saturday, June 21, from 3–6 PM. Partake in sun-drenched afternoons with live music, sweeping waterfront views, tasty bites, and crisp, refreshing beverages. The carefree rhythm of summer starts now!

Summer

Guests enjoying fire brick oven pizza and champagne on The Pointe

Memorial Day Weekend

Welcome the start of summer at Inn at Perry Cabin with live music, waterfront gatherings, and festive offerings along the Miles River!

Friday, May 22
3–6 PM | Nina Peterson | Live Music
Waterfront Fire Pits

Saturday, May 23
12–3 PM | Big Band Ensemble
The Pointe & Lighthouse
Crush Bar & Wood-Fired Pizza

Sunday, May 24
12–3 PM | Live Music
The Pointe & Lighthouse
Margaritas & Mocktails | Wood-Fired Pizza & Light Bites

CBMM Antique & Classic Boat Festival and Coastal Arts Fair

Plan ahead for the 38th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum, happening Friday-Sunday, June 19-21! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Visit here for event details and highlights.

Independence Day

Join us for a star-spangled celebration with the best seats in town! Settle into our cozy waterfront Adirondack chairs—or take to the water aboard one of our elegant vessels—for a truly unforgettable view of St. Michaels’ dazzling fireworks display.

Plein Air Easton

Plein Air Easton, celebrating its 22nd year July 10 - 19, 2026, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.

CBMM Watermen’s Appreciation Day & Crab Feast

Mark your calendars for Sunday, August 9th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen.

Couple relaxing in Adirondack's on the Manor Lawn

Labor Day Weekend

Toast to the final days of summer with a festive waterfront weekend. Details and programming forthcoming.

Talbot Humane Paws & Plates

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day! Due to the forecast, Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Sparkling Afternoons

Rum Running on the Skipjack

Join us every Wednesday from 5:30–7:00 PM through August 27 for an evening of sailing, storytelling, and handcrafted tastings from our friends at LYON Rum . This adventure is timed perfectly to catch a front-row view of the Wednesday Night Sailboat Races on the Miles River. Visit our Fleet page to learn more!

Fall

Guests enjoying an evening around waterfront firepits

Harbor Happy Hour | Live Music Series

Join us every Friday in September and October from 3–6 PM for an afternoon of live music by the water! Relax into the weekend with stunning waterfront views, small bites, and crisp, refreshing drinks in hand. Soak up the golden light of falls arrival as it dances across the river— good vibes, great company, and a front-row seat to the season’s beauty.

On Halloween Friday, begin your evening with us and enjoy house-made candies thoughtfully crafted by our culinary team—before heading out for a night of spooky fun!

Chesapeake Film Festival

The prestigious Chesapeake Film Festival returns to Easton, Maryland from October 10th - 12th! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought-provoking documentaries, and engaging discussions with industry experts.

Fall into St. Michaels

Fall into the enchantment of St. Michaels October 17 - 19! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.

Oyster Fest

Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 25th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!

Waterfowl Festival

Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 14th - 16th! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!

Market stall with glassware and people browsing under a white tent.

Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition

Mark your calendar for November 22nd, as the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, hosts the Holiday Edition of the beloved Sea Glass and Coastal Arts Festival. This seasonal celebration will showcase coastal craftsmanship at its finest, with over 90 exhibitors offering unique jewelry, home décor, art, and more—just in time for the holidays.

Under the Stars Stargazing Experience on the waterfront

ASTRO Weekend with the Sky Guy Greg!

Join us for a weekend under the stars September 27–28, led by Sky Guy Greg Redfern, NASA JPL Solar System Ambassador. Experience expert-led presentations, stunning telescope viewings, and unforgettable waterside stargazing sessions. Whether you’re an avid stargazer or simply curious about the night sky, this immersive event offers something for everyone. View the two-day itinerary here.

Upcoming Events

Winter

8th Annual St. Michaels ChocolateFest

Chesapeake Fire & Ice Festival in Easton

Nordic SPA Experience

JOIN US SUPER BOWL LX

Lighting of the Lane

Midnight Madness

Christmas in St. Michaels

Spring

Eastern Shore Sea Glass and Coastal Arts Festival

St. Michaels WineFest

Mother's Day

Easter Day Petting Zoo & Pony Rides

Return of the Fleet

Easter on the Miles

Talbot Humane Paws & Plates

Sparkling Afternoons

Summer

Memorial Day Weekend

CBMM Antique & Classic Boat Festival and Coastal Arts Fair

Independence Day

Plein Air Easton

CBMM Watermen’s Appreciation Day & Crab Feast

Labor Day Weekend

Talbot Humane Paws & Plates

Sparkling Afternoons

Rum Running on the Skipjack

Fall

Harbor Happy Hour | Live Music Series

Chesapeake Film Festival

Fall into St. Michaels

Oyster Fest

Waterfowl Festival

Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition

ASTRO Weekend with the Sky Guy Greg!

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